JP2007522287A - Composition, halogenated composition, chemical product and telomerization method - Google Patents
Composition, halogenated composition, chemical product and telomerization method Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000000126 substance Substances 0.000 title abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 10
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- 230000000737 periodic effect Effects 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 230000003797 telogen phase Effects 0.000 claims description 30
- 239000003999 initiator Substances 0.000 claims description 15
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical group FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 150000002978 peroxides Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
- C11D3/245—Organic compounds containing halogen containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/14—Acyclic saturated compounds containing halogen atoms containing fluorine and bromine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/16—Acyclic saturated compounds containing halogen atoms containing fluorine and iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
-
- C11D2111/42—
Abstract
以下の化学式、RF(RT)nQ、あるいは、式(I)、式(II)、RCl(RT)nH を有する組成物が示される。RF基は4以上のフッ素原子を有し、RT基はペンダント−CF3基を有する1以上のC-2基を含み、nは1以上、R1基は炭素原子を含み、RCl基は−CCl3を含み、Q基は元素周期表の原子を1以上含む。また、テロマー化の方法も開示される。
【選択図】図1A composition having the following chemical formula, R F (R T ) nQ, or Formula (I), Formula (II), R Cl (R T ) nH is shown. The R F group has 4 or more fluorine atoms, the R T group contains one or more C-2 groups with pendant —CF 3 groups, n is 1 or more, the R 1 group contains carbon atoms, R Cl The group includes —CCl 3 and the Q group includes one or more atoms from the periodic table. A method of telomerization is also disclosed.
[Selection] Figure 1
Description
(優先権の主張) 本出願は、2004年1月30日出願の米国仮出願番号60/540,612「フッ素官能基、フッ素組成物、フッ素添組成物の製造方法および物質の処理」に基づき優先権を主張するものであり、その全開示内容を参考として含む。
本発明は、組成物、ハロゲン化組成物、化学生成物およびテロマー化方法に関する。
(Claim of priority) This application is based on US Provisional Application No. 60 / 540,612, filed January 30, 2004, "Fluorine Functional Groups, Fluorine Composition, Method for Producing Fluorinated Composition, and Treatment of Substances". It claims priority and includes the entire disclosure content as a reference.
The present invention relates to compositions, halogenated compositions, chemical products, and telomerization methods.
界面活性剤、ポリマー、及びウレタン等の組成物はハロゲン化官能基を有している。これらの官能基は、物質の処理や物質の性能を高めるために使用される場合に前記組成物の性能に影響を与えるために組み込まれているものである。例えば、ハロゲン化官能基を含む界面活性剤は、単独あるいは水溶性フィルムフォーム(AFFF)などの形態で消火剤として使用できる。ハロゲン化官能基を有するポリマーおよび/またはウレタンも物質の処理に使用されている。これらの組成物の調製のために、ハロゲン化中間組成物を合成することができる。 Compositions such as surfactants, polymers, and urethanes have halogenated functional groups. These functional groups are incorporated to affect the performance of the composition when used to enhance the performance of the material or the material. For example, a surfactant containing a halogenated functional group can be used as a fire extinguisher alone or in the form of an aqueous film foam (AFFF). Polymers having halogenated functional groups and / or urethanes are also used for the treatment of materials. For the preparation of these compositions, halogenated intermediate compositions can be synthesized.
本発明は、RF(RT)nQおよび/または下記式で表される1種以上を含む組成物を提供する。
これらの組成物において、RF基は4以上のフッ素原子を含み、RT基は1以上のペンダント−CF3基を有するC-2基を1以上含み、nは1以上であり、R1基は1以上の炭素原子を含み、Q基は元素周期表の原子を1以上有している。またRCl(RT)nHを含む組成物も提供され、RCl基は1以上の−CCl3基を含んでいる。 In these compositions, the R F group contains 4 or more fluorine atoms, the R T group contains 1 or more C-2 groups having one or more pendant —CF 3 groups, n is 1 or more, and R 1 The group contains one or more carbon atoms, and the Q group has one or more atoms from the periodic table. Also provided is a composition comprising R Cl (R T ) nH, wherein the R Cl group comprises one or more —CCl 3 groups.
テロマー化の方法は、1以上のCF3を含有するタキソゲン(taxogen)をフッ素含有テロゲン(telogen)に曝露させてテロマーを生成し、該フッ素含有テロゲンは4以上のフッ素原子を含んでいる。 The method of telomerization involves exposing a taxogen containing one or more CF 3 to a fluorine-containing telogen to produce a telomer, the fluorine-containing telogen containing four or more fluorine atoms.
本発明の開示は、米国特許法「科学および有用技術の発展の促進」(第1条第8項)に基づいて示されている。以下に組成物ならびに組成物の製造方法について図面を参照しつつ説明する。 The disclosure of the present invention is shown based on the US Patent Law “Promoting the Advancement of Science and Useful Technologies” (Article 1, Paragraph 8). The composition and the method for producing the composition will be described below with reference to the drawings.
図は、システム10のハロゲン化組成物の製法について示したもので、タキソゲン2、テロゲン4、開始剤6を反応容器(reactor)8に供給し、テロマー9を生成する。模範的具体例では、システム10はテロマー化の方法を実行する。ある具体例によれば、タキソゲン2はテロゲン4に曝露されてテロマー9を形成する。また別の具体例ではタキソゲン2は開始剤6の存在下でテロゲン4に曝露させることもできる。反応容器8は曝露中の試薬を加熱するように構成することもできる。
The figure shows how to make a halogenated composition of system 10, in which taxogen 2, telogen 4 and initiator 6 are fed to a reactor 8 to produce
タキソゲン2は1以上のCF3含有化合物を含むことができる。CF3含有化合物は1以上のペンダント−CF3基を有するC-2基を含む。具体的には、タキソゲン2は3,3,3−トリフルオロプロペン(TFP、トリフルオロプロペン)等のオレフィン類を含む。 Taxogen 2 can include one or more CF 3 -containing compounds. CF 3 -containing compounds comprise C-2 groups having one or more pendant —CF 3 groups. Specifically, taxogen 2 contains olefins such as 3,3,3-trifluoropropene (TFP, trifluoropropene).
テロゲン4は、フッ素および/または塩素などのハロゲンを含むことができる。テロゲン4は4以上のフッ素原子を含むことができ、RFQおよび/またはRClQで表すことができる。RF基は4以上のフッ素原子を含み、Q基は元素周期表の1以上の原子を含む。該Q基は、例えばRF基が(CF3)2CF−および/または−C6F13であるとき、HまたはIであることができる。該RCl基は1以上の−CCl3基を含むことができる。テロゲンとしては具体的に、(CF3)2CFI、C6F13I、トリクロロメタン、HP(O)(OEt)2、BrCFClCF2Br、R−SH(Rは炭素含有する基)、および/またはMeOHを例示できる。タキソゲン2としてはトリフルオロプロペンを、テロゲン4としては(CF3)2CFIを例示でき、タキソゲン2対テロゲン4のモル比は約1:1から約1:10、1:4から約4:1、そして/または約2:1から約4:1である。 Telogen 4 can include halogens such as fluorine and / or chlorine. Telogen 4 can contain 4 or more fluorine atoms and can be represented by R F Q and / or R Cl Q. The R F group contains 4 or more fluorine atoms, and the Q group contains 1 or more atoms of the periodic table. The Q group can be H or I, for example when the R F group is (CF 3 ) 2 CF— and / or —C 6 F 13 . The R Cl group can include one or more —CCl 3 groups. Specific examples of the telogen include (CF 3 ) 2 CFI, C 6 F 13 I, trichloromethane, HP (O) (OEt) 2 , BrCFClCF 2 Br, R—SH (R is a group containing carbon), and / or Or MeOH can be illustrated. Taxogen 2 can be exemplified by trifluoropropene, and telogen 4 can be exemplified by (CF 3 ) 2 CFI, wherein the molar ratio of taxogen 2 to telogen 4 is about 1: 1 to about 1:10, 1: 4 to about 4: 1. And / or from about 2: 1 to about 4: 1.
反応容器8は実験的、産業的スケールであって、具体例として、試薬を内包して温度制御するように構成してもよい。より具体的には、反応容器8は、試薬を反応させている間に約130℃から約150℃の加熱ができるものである。 The reaction vessel 8 is an experimental and industrial scale. As a specific example, the reaction vessel 8 may be configured to contain a reagent and control the temperature. More specifically, the reaction vessel 8 can be heated from about 130 ° C. to about 150 ° C. during the reaction of the reagent.
タキソゲン2にテロゲン4を曝露して生成するテロマー9は、RF(RT)nQおよび/またはRCl(RT)nHを含むことができる。RT基は、例えば下式で表されるような基で、ペンダント−CF3基を有する1以上のC-2基を含むことができる。
生成物は具体的には、下式で表される化合物、
より具体的には、nは1以上、或いは2以上で、下記の生成物を1以上含む。
さらに具体例として、タキソゲンとしてトリフルオロプロペンを、テロゲンとしての(CF3)2CFIに曝露すると、下式のテロマーを形成できる。
別の具体例として、トリフルオロプロペンを、テロゲンとしてのC6F13Iに曝露すると、下式のテロマーを形成できる。
また別の具体例として、トリフルオロプロペンを、テロゲンとしてのCCl3Z(Z=H,Br,Clなど)に曝露すると、下式のテロマーを形成できる。
nが2以上である生成物はテロゲンに対して過剰のタキソゲンを反応させたときに形成される。例えば、タキソゲン:テロゲンのモル比が2:1以上であるときは、nが2以上の生成物を得ることができる。具体的例としては、タキソゲンとして2モル以上のトリフルオロプロペンに、テロゲンとして1モル以上の(CF3)2CFIを曝露させると、下式のテロマーの一方または双方が形成されるのである。
さらに具体例としてあげると、開始剤6を試薬を反応させている反応容器8内に供給することもできる。開始剤6としては、熱、光化学(UV)、ラジカル、または金属錯体などで、ジ−t−ブチルパーオキシドなどの過酸化物をも含む。開始剤6はCuなどの触媒も含み得る。開始剤6とテロゲン4はともに反応容器8に供給され、タキソゲン2に対して開始剤6のモル比は、約0.001〜0.05であり、好ましくは約0.01〜0.03である。 As a specific example, the initiator 6 can be supplied into the reaction vessel 8 in which the reagent is reacted. The initiator 6 is a heat, photochemistry (UV), radical, or metal complex, and also includes a peroxide such as di-t-butyl peroxide. Initiator 6 may also include a catalyst such as Cu. Initiator 6 and telogen 4 are both supplied to reaction vessel 8, and the molar ratio of initiator 6 to taxogen 2 is about 0.001 to 0.05, preferably about 0.01 to 0.03. is there.
種々の開始剤6、テロゲン4を用いてタキソゲン2をテロマー化した結果を表1に示した。テロマー化は、光化学および/または金属錯体開始剤6を用いて、カリウス(Carius)の反応管8を用いてバッチ条件で反応させた。また熱および/または過酸化物開始剤6を用いたテロマー化は、160および/または500cm3のハステロイ(Hastelloy)の反応容器8を用いた。テロゲン4(そのまま或いは過酸化物溶液として)は約60℃〜180℃の温度でガス状態で供給し、表1に示すように、テロゲン4[T]0/タキソゲン2[Tx]0の開始時のモル比R0は0.25〜1.5の範囲で種々変動させ、反応時間は4〜24時間である。生成混合物はガスクロマトグラフィーで分析し、或いはまた生成物を蒸留分画して1H−NMR、19F-NMR、13C−NMRによって分析できる。モノアダクト(n=1)およびジアダクト(n=2)は表1に示すように生成した。 The results of telomerization of taxogen 2 using various initiators 6 and telogen 4 are shown in Table 1. Telomerization was reacted in batch conditions using a reaction tube 8 from Carius with photochemical and / or metal complex initiator 6. Also, telomerization using heat and / or peroxide initiator 6 was performed using a Hastelloy reaction vessel 8 of 160 and / or 500 cm 3 . Telogen 4 (as is or as a peroxide solution) is supplied in a gas state at a temperature of about 60 ° C. to 180 ° C., and as shown in Table 1, at the start of telogen 4 [T] 0 / taxogen 2 [Tx] 0 The molar ratio R 0 is varied in the range of 0.25 to 1.5, and the reaction time is 4 to 24 hours. The product mixture can be analyzed by gas chromatography, or alternatively the product can be distilled and analyzed by 1 H-NMR, 19 F-NMR, 13 C-NMR. Monoadducts (n = 1) and diaducts (n = 2) were produced as shown in Table 1.
Claims (28)
RF基は4以上のフッ素原子を含み、
RT基は、1以上のペンダント−CF3基を有する1以上のC-2基を含み、
nは1以上であり、
Q基は元素周期表の原子を1以上有していることを特徴とする組成物。 A composition comprising R F (R T ) nQ comprising:
The R F group contains 4 or more fluorine atoms;
The RT group comprises one or more C-2 groups having one or more pendant —CF 3 groups;
n is 1 or more,
The Q group has one or more atoms of the periodic table of elements.
RF基は4以上のフッ素原子を含み、
R1基は1以上の炭素原子を含み、
nは1以上であり、
Q基は元素周期表の原子を1以上有していることを特徴とする組成物。
The R F group contains 4 or more fluorine atoms;
The R 1 group contains one or more carbon atoms;
n is 1 or more,
The Q group has one or more atoms of the periodic table of elements.
RCl基は1以上の−CCl3を含み、
RT基は、1以上のペンダント−CF3基を有する1以上のC-2基を含み、
nは1以上であることを特徴とする組成物。 A composition comprising R Cl (R T ) nH comprising:
The R 2 Cl group comprises one or more —CCl 3 ;
The RT group comprises one or more C-2 groups having one or more pendant —CF 3 groups;
n is 1 or more, The composition characterized by the above-mentioned.
テロマーが下式で表され、
nは1以上であり、
Q基は元素周期表の原子を1以上有していることを特徴とする請求項18記載の方法。 The CF 3 -containing taxogen is trifluoropropene,
The telomer is represented by the following formula,
n is 1 or more,
The method according to claim 18, wherein the Q group has one or more atoms of the periodic table.
フッ素含有テロゲンが(CF3)2CFIであり、
タキソゲン:テロゲンが2:1〜4:1のモル比であることを特徴とする請求項18記載の方法。 The CF 3 -containing taxogen is trifluoropropene,
The fluorine-containing telogen is (CF 3 ) 2 CFI;
19. The method of claim 18, wherein taxogen: telogen is in a molar ratio of 2: 1 to 4: 1.
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2005
- 2005-01-28 KR KR1020077021382A patent/KR20070101402A/en not_active Application Discontinuation
- 2005-01-28 KR KR1020077029701A patent/KR20080009760A/en not_active Application Discontinuation
- 2005-01-28 KR KR1020077029422A patent/KR20080012974A/en not_active Application Discontinuation
- 2005-01-28 KR KR1020067015480A patent/KR20060132889A/en not_active Application Discontinuation
- 2005-01-28 EP EP05712170A patent/EP1718587A4/en not_active Withdrawn
- 2005-01-28 WO PCT/US2005/002617 patent/WO2005074528A2/en active Application Filing
- 2005-01-28 CN CNA2005800107135A patent/CN1957078A/en active Pending
- 2005-01-28 CN CNA2005800107506A patent/CN1965067A/en active Pending
- 2005-01-28 KR KR1020067015478A patent/KR20070001117A/en not_active Application Discontinuation
- 2005-01-28 US US10/587,344 patent/US20070276167A1/en not_active Abandoned
- 2005-01-28 CA CA002554029A patent/CA2554029A1/en not_active Abandoned
- 2005-01-28 CN CNA2005800108072A patent/CN1960958A/en active Pending
- 2005-01-28 JP JP2006551480A patent/JP2007522287A/en active Pending
- 2005-01-31 AR ARP050100357A patent/AR048062A1/en not_active Application Discontinuation
- 2005-01-31 AR ARP050100356A patent/AR048402A1/en not_active Application Discontinuation
-
2007
- 2007-11-20 US US11/986,222 patent/US20080076948A1/en not_active Abandoned
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AR048402A1 (en) | 2006-04-26 |
CN1957078A (en) | 2007-05-02 |
KR20070101402A (en) | 2007-10-16 |
EP1718587A2 (en) | 2006-11-08 |
KR20070001117A (en) | 2007-01-03 |
CN1965067A (en) | 2007-05-16 |
KR20080012974A (en) | 2008-02-12 |
US20070276167A1 (en) | 2007-11-29 |
WO2005074528A2 (en) | 2005-08-18 |
CA2554029A1 (en) | 2005-08-18 |
EP1718587A4 (en) | 2008-02-20 |
WO2005074528A3 (en) | 2005-12-22 |
US20080076948A1 (en) | 2008-03-27 |
CN1960958A (en) | 2007-05-09 |
KR20080009760A (en) | 2008-01-29 |
KR20060132889A (en) | 2006-12-22 |
AR048062A1 (en) | 2006-03-29 |
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